ES2385249T3 - Polymers containing amide for rheology control - Google Patents

Abstract

Amide-containing polymers of the general formula (I) AX-CO- (CH2) 2-NR1-R2- [Y-R3-Y-R4] aB (I) as well as their salts with carboxylic acids, phosphoric acid esters and acids sulfonic, in which A represents R5 or R6-Y- [R4-Y-R3-Y] b-R2-NR 1- (CH2) 2-CO-X-R7 and B represents Y-R6 or NR1- (CH2) 2 -CO-X-R5, and where R1 represents H, (CH2) 2-CO-X-R5 and / or CONH-R 'with R'> = R8 or -C6H3 (CH3) -NHCOO-R8, R2, R3, R4 and R7 independently of each other represent a C1-C40 alkylene moiety, C3-C40 alkenylene, C5-C40 cycloalkylene, arylene, C7-C40 aralkylene or polyoxyalkylene or a polyester moiety, R5 represents H, a C1-C22 alkyl moiety, aryl , C7-C12 aralkyl, C5-C12 cycloalkyl, hydroxyalkyl or N, N'-dialkylamino, a hydroxyl moiety, C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-aralkoxy-polyoxyalkylene, or a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkanol, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12 aralkoxy-polyoxyalkylene, R6 repres enta a C1-C30 alkyl, C3-C22 alkenyl, hydroxyalkyl, C4-C13 cycloalkyl, aryl or C7-C12 aralkyl moiety, R8 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl or C5-C12 cycloalkyl moiety, a moiety C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy, a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkanol or C7-C12 alkoxyol or a C1-C22 alkoxy initiated, C6-C12 cycloalkoxy or aralkoxy polyester C7-C12-polyoxyalkylene, X represents the same or different O, NH or NR9 moieties, R9 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl, hydroxyalkyl, C5-C12 cycloalkyl moiety, Y represents one or more of the following groups COO, OCO, NHCO, CONH, NHCOO, OOCNH, NHCONH and b independently from each other represent a number from 1 to 19.

Description

Polymers containing amide for rheology control

The invention relates to amide-containing polymers for the rheology control of liquid polymeric systems such as, for example, solvent-free, solvent-free and aqueous lacquers, PVC plastisols, epoxy-based coatings and unsaturated polyester resins.

Silicon acids, hydrated castor oil or organically modified bentonites are frequently used to control the rheology of liquid systems, as described, for example, in US 4,208,218, US

4,410,364 and US 4,412,018. In addition, polyamide waxes are frequently used. In the field of polyamides and polyamide esters there are numerous patents, such as, for example, EP 0 692 509, EP 0277420, EP 0528363 EP 0239419, US 5,510,452 and US 5,349,011. But combinations of bentonites modified with polyamides are also used, as described in EP 0509202 and EP 0826750.

In these substances it is disadvantageous that in most cases they represent dried pastes or solids, which must be broken down by means of solvents and the application of shear forces to give a semi-finished product,

or they must be incorporated by means of a directed temperature control in, for example, liquid coating systems. If the necessary temperatures are not maintained, crystalline units appear in the finished coating system, which leads to coating failures. The disadvantage generated by these substances is that they lead to turbidity and cloud formations (haze) in clear, transparent coatings. In addition, the handling of dry products that produce dust during processing is not desirable.

While polyamide esters are often liquid, however they are clearly less effective than naturally occurring solid substances.

Other solutions for rheology control were set forth in EP 0 198 519. In this document an isocyanate is reacted with an amine in the presence of binders to give a urea, which in the finest dispersed form forms acicular crystals. These binders thus modified are offered as binders that control rheology and prevent sagging, and are called "sag control agents".

The disadvantage of these products is that they are always attached to the binders in which they produced and therefore a subsequent universal correction of the finished systems is not possible.

EP 0 006 252 describes a process for the production of a thixotropic agent, which solves some of the disadvantages mentioned above by providing urea-urethanes, which occur in aprotic solvents in the presence of LiCl by the reaction of isocyanate adducts. with polyamines. The disadvantage of the products thus produced lies in the indefinite structure conditioned by the urea-urethane production process. In said process diisocyanates and monoalcohols are used in equal molar amounts. In this respect, both NCO-functional monoadducts and non-NCOfunctional diaducts are generated. In addition, a certain percentage of monomeric diisocyanate remains unreacted. The percentages of the different products fluctuate, according to the accessibility of the NCO group and the control of the applied reaction, such as temperature and time. However, all adducts thus produced contain high amounts of unreacted diisocyanate, which in the additional reaction with polyamines leads to an elongation of the uncontrolled chain of the molecule. These products then tend to experience phenomena of premature precipitation or gelation and therefore to the formation of so-called "bites" ("seeds") in the binder. In US 6,420,466 these disadvantages are avoided by removing the excess isocyanate. However, the products described therein have the disadvantage that they only provide stable solutions in very polar solvents such as, for example, N-methylpyrrolidone (NMP) with the aid of alkaline salts.

Therefore, the present invention is based on the objective of providing products, which are suitable for the rheology control of liquid polymer systems, comprise polymers of a defined structure and thus guarantee a better action profile and better reproducibility of the control of rheology, and that in particular avoid the disadvantages illustrated above of the state of the art additives.

Surprisingly it was found that these objectives are solved by providing polymers containing amide of general formula (I)

A-X-CO- (CH2) 2-NR1-R2- [Y-R3-Y-R4] a-B (I)

as well as its salts with carboxylic acids, esters of phosphoric acids and sulfonic acids,

in which

A represents R5 or R6-Y- [R4-Y-R3-Y] b-R2-NR1- (CH2) 2-CO-X-R7 and

B represents Y-R6 or NR1- (CH2) 2-CO-X-R5, and in which

R1 represents H, (CH2) 2-CO-X-R5 and / or CONH-R ’with R’ = R8 or -C6H3 (CH3) -NHCOO-R8,

R2, R3, R4 and R7 independently of each other represent a C1-C40 alkylene, C3-C40 alkenylene, C5-C40 cycloalkylene, arylene, C7-C40 aralkylene or polyoxyalkylene radical or represent a polyester moiety,

R5 represents H, a C1-C22 alkyl, aryl, C7-C12 aralkyl, C5-C12 cycloalkyl, N or N'dialkylamino moiety, a hydroxyl, C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-aralkoxy moiety polyoxyalkylene, or a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkanol, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12 aralkoxy-polyoxyalkylene,

R6 represents a C1-C30 alkyl, C3-C22 alkenyl, hydroxyalkyl, C4-C13 cycloalkyl, aryl or C7-C12 aralkyl moiety,

R8 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl or C5-C12 cycloalkyl moiety, a C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy moiety, a polyester initiated with C1-C22 alkanol, cycloalkane C5-C12 or C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C6-C12 cycloalkoxy or C7-C12 aralkoxy-polyoxyalkylene,

X represents the same or different Subtract O, NH or NR9 residues,

R9 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl, hydroxyalkyl, C5-C12 cycloalkyl moiety,

Y represents one or more of the following groups COO, OCO, NHCO, CONH, NHCOO, OOCNH, NHCONH and

a and b independently of each other represent a number from 1 to 19.

The definitions of residues A, B, R1, R2, R3, R4, R5, R6, R7, R8, R9, R ', X and Y as well as indices a and b correspond in the context of this invention, regardless of compounds in which they are present, to the previous definitions. Preferred embodiments of these moieties are found in the respective dependent claims.

In the event that one or more of the radicals R2, R3, R4, R5, R7 and / or R8 contain a polyoxyalkylene fraction, these moieties, independently of the compounds in which they appear, are preferably constituted by oxide units of ethylene, propylene oxide and / or butylene oxide, arranged statistically or in blocks, and if necessary one or more of these units are replaced by styrene units. Especially preferred are ethylene oxide and propylene oxide moieties.

In the event that one or more of the radicals R2, R3, R4, R5, R7 and / or R8 comprise a polyester moiety, these moieties, regardless of the compounds in which they appear, are preferably constituted on the basis of one or more C1-C18 hydroxycarboxylic acids or one or more lactones, such as β-propiolactone, δ-valerolactone, ε-caprolactone and ε-caprolactone substituted with C1-C6 alkyl.

Residues R1 represent H, (CH2) 2-CO-X-R5 and / or CONH-R 'with R = R8 or -C6H3 (CH3) -NHCOO-R8, such as, for example, CONH-C18H37 and / or CONH-C6H3 (CH3) -NHCOOC4H9.

The R2 and R4 moieties independently from each other preferably represent a C2-C18 alkylene moiety, C7-C15 aralkylene, especially preferably a C2-C12 alkylene moiety, C7-C12 aralkylene, most particularly preferably a C2-alkylene moiety C8, C7-C9 aralkylene, such as, for example, a hexamethylene, octamethylene or m-xylylene moiety. Preferably residues R2 and R4 are identical.

R3 represents a C2-C40 alkylene, C3-C40 alkenylene, C5-C40 cycloalkylene, C7-C40 arylene or aralkylene, preferably a C30-C40 alkylene, C30-C40 alkenylene, C30-C40 cycloalkylene, C30-C40 arylene or aralkylene , such as, for example, the remainder between the two carboxylic acid groups of the dimeric acid. Especially preferably R3 represents a C34 moiety.

R5 preferably represents a C1-C22 alkyl moiety, a hydroxyl moiety or an alkoxypolyoxyalkylene moiety.

R6 preferably represents a C1-C30 alkyl moiety or a C3-C22 alkenyl moiety, especially preferably a C12-C30 alkyl moiety or a C12-C22 alkenyl moiety and most particularly preferably a C12-C20 alkyl moiety or an alkenyl moiety C12-C20, such as, for example, a C17 alkyl moiety or a C17 alkenyl moiety.

R7 preferably represents a C1-C18 alkylene moiety or a polyoxyalkylene moiety and R8 a C1-C22 alkyl moiety. X preferably represents the same or different O or NH moieties, and Y preferably one or more of the NHCO and CONH groups.

Indices a and b independently of each other represent a number from 1 to 19, so

especially preferable from 2 to 7, and are preferably identical. Especially preferred embodiments of the invention refer to compounds of general formula (I) with A = R5 and B = NR1- (CH2) 2-CO-X-R5, resulting in the general formula (II):

R5-X-CO- (CH2) 2-NR1-R2- [Y-R3-Y-R4] a-NR1- (CH2) 2-CO-X-R5 (II), compounds of general formula (I) with A = R5 and B = Y-R6, from which the general formula (III) results:

R5-X-CO- (CH2) 2-NR1-R2- [Y-R3-Y-R4] aY-R6 (III), and compounds of general formula (I) with A = R6-Y- [R4-Y -R3-Y] a-R2-NR1- (CH2) 2-CO-X-R7 and B = Y-R6, resulting in the general formula (IV):

R6-Y- [R4-Y-R3-Y] a-R2-NR1- (CH2) 2-CO-X-R7-X-CO- (CH2) 2-NR1-R2- [Y-R3-Y- R4] aY-R6 (IV) The present invention also relates to amide-containing polymers, also to a process for the production of amide-containing polymers of general formula (I)

AX-CO- (CH2) 2-NR1-R2- [Y-R3-Y-R4] aB (I) as well as its salts with carboxylic acids, esters of phosphoric acids and sulphonic acids, in which A represents R5 or R6 -Y- [R4-Y-R3-Y] b-R2-NR1- (CH2) 2-CO-X-R7 and B represents Y-R6 or NR1- (CH2) 2-CO-X-R5, and in which R1 represents H, (CH2) 2-CO-X-R5 and / or CONH-R 'with R' = R8 or -C6H3 (CH3) -NHCOO-R8, R2, R3, R4 and R7 independently of each other represent a C1-C40 alkylene moiety, C3-C40 alkenylene, cycloalkylene

C5-C40, arylene, C7-C40 aralkylene or polyoxyalkylene or a polyester moiety, R5 represents H, a C1-C22 alkyl, aryl, C7-C12 aralkyl, C5-C12 cycloalkyl, N or N'dialkylamino moiety, a hydroxyl, C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-aralkoxy moiety polyoxyalkylene, or a polyester

initiated with C1-C22 alkanol, C5-C12 cycloalkanol, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy, R6 represents a C1-C30 alkyl, C3-C22 alkenyl, hydroxyalkyl, C4-C13 cycloalkyl, aryl or C7-C12 aralkyl moiety, R8 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl or C5-C12 cycloalkyl moiety, a C1-C22 alkoxy moiety,

C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy, a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkane or C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C6-C12 cycloalkoxy or C7-C12 aralkoxy-polyoxyalkylene, X represents the same or different O, NH or NR9 moieties, R9 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl, hydroxyalkyl, C5-C12 cycloalkyl moiety, Y represents one or more of the following groups COO, OCO, NHCO, CONH, NHCOO, OOCNH, NHCONH and a and b independently of each other represent a number from 1 to 19, in which,

(A) one or more compounds of general formulas (V) and (VIII)

H2N-R2- [Y-R3-Y-R4] a-NH2 (V)

H2N-R2- [Y-R3-Y-R4] to-YR6 (VIII)

they are reacted with one or more compounds of general formulas (VI) and (IX) R5-X-CO-CH = CH2 (VI) 5 H2C = HC-CO-X-R7-X-CO-CH = CH2 (IX) forming compounds with R1 = hydrogen,

used for 1 mole of NH2 groups in the compounds of general formulas (V) and (VIII) of 0.8 to 1.2 moles of groups CH = CH2 in the compounds of formulas (VI) and (IX), and

(B) in the case where R1 represents totally or partially (CH2) 2-CO-X-R5 and / or CONH-R ', the compounds of step 10 (A) are reacted with one or more compounds of general formulas (VI) and (VII) R5-X-CO-CH = CH2 (VI) R'-NCO (VII),

using for 1 mole of NR1 groups in the compounds of step (A) up to 1.2 moles of compounds of general formula (VI) and / or (VII), and

(C) in the case where in the case of the compounds of the general formula (I) it is salts of carboxylic acids, esters of phosphoric acids and sulphonic acids, a reaction of the compounds of step (A) takes place. or (B) with carboxylic acids, esters of phosphoric acids and sulfonic acids.

In a preferred embodiment

20 (A) one or more compounds of general formula (V)

H2N-R2- [Y-R3-Y-R4] a-NH2 (V)

they are reacted with one or more compounds of the general formula (VI) R5-X-CO-CH = CH2 (VI)

forming compounds with R1 = hydrogen,

Using for 1 mol of NH2 groups in the compounds of general formula (V) of 0.8 to 1.2 moles of groups CH = CH2 in the compounds of formula (VI), and

(B) in the case where R1 represents totally or partially (CH2) 2-CO-X-R5 and / or CONH-R ', the compounds of step (A) are reacted with one or more compounds of formulas general (VI) and (VII) 30 R5-X-CO-CH = CH2 (VI)

R’-NCO (VII), with up to 1.2 moles of compounds of general formula (VI) and / or (VII) being used for 1 mole of NR1 groups in the compounds of step (A), and

(C) for the case in which in the case of the compounds of general formula (I) it is acid salts

Carboxylic esters of phosphoric acids and sulfonic acids, a reaction of the compounds of step (A) or (B) with carboxylic acids, esters of phosphoric acids and sulfonic acids takes place.

In a further preferred embodiment

(A) one or more compounds of the general formula (VIII)

H2N-R2- [Y-R3-Y-R4] to-YR6 (VIII)

they are reacted with one or more compounds of the general formula (VI) 5 R5-X-CO-CH = CH2 (VI) forming compounds with R1 = hydrogen,

used for 1 mol of NH2 groups in the compounds of general formula (VIII) of 0.8 to 1.2 moles of CH = CH2 groups in the compounds of formula (VI), and

(B) in the case where R1 represents totally or partially (CH2) 2-CO-X-R5 and / or CONH-R ', the compounds of step 10 (A) are reacted with one or more compounds of general formulas (VI) and (VII) R5-X-CO-CH = CH2 (VI) R'-NCO (VII),

using for 1 mole of NR1 groups in the compounds of step (A) up to 1.2 moles of compounds of general formula (VI) and / or (VII), and

(C) in the case where in the case of the compounds of the general formula (I) it is salts of carboxylic acids, esters of phosphoric acids and sulphonic acids, a reaction of the compounds of step (A) takes place. or (B) with carboxylic acids, esters of phosphoric acids and sulfonic acids.

In a further preferred embodiment

20 (A) one or more compounds of the general formula (VIII)

H2N-R2- [Y-R3-Y-R4] to-YR6 (VIII)

They are reacted with one or more compounds of the general formula (IX) H2C = HC-CO-X-R7-X-CO-CH = CH2 (IX)

forming compounds with R1 = hydrogen,

For 1 mol of NH2 groups in compounds of general formula (VIII) of 0.8 to 1.2 moles of CH = CH2 groups in compounds of formula (IX), and

(B) in the case where R1 represents totally or partially (CH2) 2-CO-X-R5 and / or CONH-R ', the compounds of step (A) are reacted with one or more compounds of formulas general (VI) and (VII) 30 R5-X-CO-CH = CH2 (VI)

R’-NCO (VII), with up to 1.2 moles of compounds of general formula (VI) and / or (VII) being used for 1 mole of NR1 groups in the compounds of step (A), and

(C) for the case in which in the case of the compounds of general formula (I) it is acid salts

Carboxylic esters of phosphoric acids and sulfonic acids, a reaction of the compounds of step (A) or (B) with carboxylic acids, esters of phosphoric acids and sulfonic acids takes place.

In the mentioned preferred embodiments of the process according to the invention the amount indicated in step (B) of the compounds of general formula (VI) can be used instead of in step (B), already in step (A) in addition of the amount indicated in step (A) of the compounds of general formula (VI).

The reaction in step (A) is preferably carried out at a temperature of from 60 to 100 ° C, especially preferably at a temperature of from 70 to 90 ° C.

The reaction in step (B), is carried out in the case of the reaction with compounds of general formula (VII) preferably at a temperature of from 50 to 100 ° C, especially preferably from 60 to 80 ° C and in the case of the reaction with a compound of general formula (VI) at a temperature of preferably from 60 to 100 ° C, especially preferably from 70 to 90 ° C.

The procedure according to the invention is explained below in specific examples.

Compounds of formula (II) with R1 = -H, - (CH2) 2-CO-X-R5, -CONH-R 'with R' = R8 or -C6H3 (CH3) -NHCOOR8 can be produced, for example, by making react one or more compounds of general formula (V):

H2N-R2- [Y-R3-Y-R4] a-NH2 (V)

wherein R2, R3 and R4 independently of each other represent a C2-C40 alkylene, C3-C40 alkenylene, C5-C40 cycloalkylene, arylene, C7-C40 aralkylene or polyoxyalkylene radical,

Y represents one or more of the following groups COO, OCO, NHCO, CONH, NHCOO, OOCNH, NHCONH, and

a represents a number from 1 to 19,

with one or more compounds of the general formula (VI):

R5-X-CO-CH = CH2 (VI)

wherein R5 represents H, a C1-C22 alkyl, aryl, C7-C12 aralkyl, C5-C12 cycloalkyl, hydroxyalkyl or N, N'dialkylamino moiety, a hydroxyl, C1-C22 alkoxy, C5-C12 alkoxy or C7 aralkoxy moiety -C12-polyoxyalkylene, in the case of the oxyalkylene moiety of ethylene oxide, propylene or butylene, including mixtures thereof, and parts of the oxyalkylene moiety may be substituted by styrene oxide or a polyester initiated with C1-C22 alkanol, C5 cycloalkane- C12, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy based on, for example, C1-C18 hydroxycarboxylic acids or lactones such as, for example, β-propiolactone , δ-valerolactone, ε-caprolactone or ε-caprolactone substituted with C1-C6 alkyl, including mixtures thereof,

X represents O, NH or NR9, and

R9 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl, hydroxyalkyl, C5-C12 cycloalkyl moiety,

and then the product is reacted if necessary with compounds of general formula (VII):

R’-NCO (VII)

in which R ’represents R8 or -C6H3 (CH3) -NHCOO-R8 and

R8 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl or C5-C12 cycloalkyl moiety, a C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-aralkoxy-polyoxyalkylene radical,

in the case of the oxyalkylene moiety of ethylene oxide, propylene or butylene oxide, including mixtures thereof, and parts of the oxyalkylene moiety are substituted, if necessary, by styrene oxide, a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkane or aralcanol C7-C12 or a polyester initiated with C1-C22 alkoxy, C6-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy based on, for example, C1-C18 hydroxycarboxylic acids or lactones such as, for example, β-propiolactone, δ-valerolactone, ε-caprolactone or ε-caprolactone substituted with C1-C6 alkyl, including mixtures thereof.

The intermediate compounds according to the invention (V) can be obtained, for example, by reacting polycarboxylic acids, preferably dicarboxylic acids, and / or dicarboxylic acid anhydrides with diamines, the diamine ratio with respect to polycarboxylic acid being increased to 2 with respect to 1 to 20 with respect to 19, especially preferably 3 with respect to 2 to 8 with respect to 7.

In the case of diamines, they are preferably aliphatic and araliphatic primary diamines, such as, for example, ethylenediamine, neopentandiamine, 1,2- and 1,3-propanediamine, 1,4-butandiamine, 1,5-pentandiamine, 1 , 6-hexamethylenediamine (also as a solution in water), 1,8-octamethylenediamine, 1,12-dodecamethylenediamine, cyclohexyldiamine, 4,4'-diaminodicyclohexylmethane, 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane, isophorondiamine, 4,7-dioxadecan -1,10-diamine, 4,11-dioxatetradecan-1,14-diamine, 4,7,10-trioxadecan-1,13-diamine, polyoxyalkylenediamines, which contain ethylene oxide and / or propylene oxide groups, arranged statistically or by blocks, they have a number average molecular weight of from 148 to 4000 g / mol and, for example, can be obtained as Jeffamine® D and Jeffamine® ED from Huntsman, polytetrahydrofuranediamines as well as para and meta-xylylenediamine. Preferably 1,6-hexamethylenediamine, 1,8-octamethylenediamine and metaxylenediamine are used. Amines of the H2N-R-NRR-NH2 type can also be used, R independently representing C1-C18 alkyl or C1-C4 alkoxy. An example of this is N, N’-bis- (3-aminopropyl) methylamine. But dihydrazides such as, for example, oxalic acid dihydrazide, succinic acid dihydrazide or adipic acid dihydrazide can also be used. The use of mixtures of diamines, also with dihydrazides, is also possible. The diamines can also be used as carbonate compounds, which during the condensation reaction react with the polycarboxylic acids with water separation and CO2 removal to give the preferred amide groups according to the invention.

In the case of polycarboxylic acids, they are preferably saturated or unsaturated, linear or branched, aliphatic, cycloaliphatic or aromatic dicarboxylic acids with at least 2, especially preferably from 3 to 40 C atoms. Examples of such polycarboxylic acids are acidic. adipic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, pimelic acid, subic acid, sebacic acid, azelaic acid, undecanedioic acid, 1,11-undecanedicarboxylic acid, dodecanedioic acid, hexadecanedioic acid, docosanodioic acid, maleic acid, fumic acid , terephthalic acid or isophthalic acid, alone or in mixtures. Acid anhydrides such as maleic acid anhydride, glutaric acid anhydride, phthalic acid anhydride and succinic acid anhydride, which if necessary are modified with alkyl or alkylene groups, for example, dodecenylsuccinic acid anhydride, are also included in the invention. Polymeric polycarboxylic acids such as, for example, polybutadiene dicarboxylic acid may also be used, as well as hydroxy functional polycarboxylic acids such as, for example, tartaric acid, citric acid and hydroxyxtallic acid. Oxydicarboxylic acids such as 3,6,9-trioxyundecanedioic acid and polyglycolic diacid are also included. Dimerized fatty acids, known to those skilled in the art as dimeric acids, with a carbon length of 36 C atoms, are particularly preferred. These dimeric acids may have both a reduced monomer content (usually <8 weight percent). ), as a percentage not exceeding 25 percent by weight of trimeric acid.

The polycarboxylic acids can be partially substituted by diisocyanates and the diamines partially by diols, then there may be ester, urethane and / or urea groups in addition to the preferred amide groups in the compounds of general formula (V).

In the case of the diols, they are, alone or in mixtures, preferably of polyoxyalkylenediols, polyoxyalkenyl diols, which if necessary are modified with alkoxy and / or C1-C4 alkyl groups, of polyether diols, polyether polyoxyalkylenediols, polylactonadioles, polyoxyalkylenediocyles, polyoxyalkylene polyols polyolefinadiols, polyacrylate diols, bisphenol A-alkoxylated diols, of diols of the α-di-dihydroxyalkylene siloxanes type as their alkoxylated compounds with an average molecular weight Mn of from 250 to 5000 g / mol.

As diisocyanates, preferably aliphatic, cycloaliphatic and aromatic diisocyanates, or mixtures thereof can be used. Examples of such diisocyanates are tetramethylene 1,4-diisocyanate, hexamethylene 1,6-diisocyanate, 2,2,4-trimethyl hexamethylene-1,6-diisocyanate, 1,10-decamethylene diisocyanate, 1,4-diisocyanate of cyclohexylene, p-phenylene diisocyanate, m-phenylene diisocyanate, toluylene 2,6-diisocyanate, toluylene 2,4-diisocyanate and mixtures thereof, py m-xylylene diisocyanate, naphthylene diisocyanate, diisocyanate of isophorone, 4-4'-diisocyanatodicyclohexylmethane, bisphenylene-4,4'-diisocyanate of 3,3'-dimethyl, 3,3'-dimethyl-diisocyanodiphenylmethane, the isomeric mixtures 2,4 'and 4-4'-diisocyanatodiphenylmethane and diisocyanate C36 dimeric.

Compounds of general formula (V) are produced under conditions known to those skilled in the art. The reaction temperature during the condensation reaction of the dicarboxylic acids with diamines or diols is preferably at 100 to 250 ° C, especially preferably at 140 to 200 ° C. The ratio of diamine and polycarboxylic acid is selected such that for n equivalents of polycarboxylic acid (n + 1) equivalents of diamine are used, so that the condensation product has an amine index of preferably 5 to 180 and so especially preferable from 15 to 100, with respect to 100% active substance.

As compounds of general formula (VI), when X represents O, acrylic acid as well as its salts, such as, for example, sodium acrylate, potassium acrylate or ammonium acrylate, and alkyl esters of alcohol acrylic acid are used linear, branched or cycloaliphatic with 1 to 22 C atoms such as, for example, methyl acrylate, ethyl acrylate, n-propyl acrylate, iso-propyl acrylate, n-butyl acrylate, isobutyl acrylate, acrylate of tert-butyl, pentyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, acrylate

of iso-octyl, 3,5,5-trimethylhexyl acrylate, octildecyl acrylate, isodecyl acrylate, lauryl acrylate, tridecyl acrylate, C16 / C18 alkyl acrylate, stearyl acrylate, behenyl acrylate, cyclohexyl acrylate, cyclohexyl acrylate Tetrahydrofurfuryl acrylate, 2-norbornyl acrylate, isobornyl acrylate, dicyclopentadienyl acrylate, dihydrodicyclopentadienyl acrylate and benzyl acrylate. Also included are aryl esters of acrylic acid such as, for example, phenyl acrylate or 2-phenoxyethyl acrylate. The use of hydroxyalkyl esters of the acrylic acid of linear, branched or cycloaliphatic diols with from 2 to 36 C atoms, such as, for example, 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 4-hydroxybutyl acrylate is also possible , as well as the use of hydroxyalkyl acrylates modified with caprolactone and / or valerolactone, with an average molecular weight Mn of from 220 to 1200, hydroxyacrylates being derived preferably from linear, branched or cycloaliphatic diols with from 2 to 8 C atoms Polyoxyalkylene acrylates, such as polyoxyethylene acrylates, polyoxypropylene acrylates or polyoxybutylene acrylates, mixed polyoxyethylene polyoxypropylene acrylates or mixtures of polyoxyethylene acrylates and polyoxypropylene acrylates with oxydroxyl acrylates with oxydroxyl acrylates at 100 C atoms they are used both in OH-functional form and with the ends occupied with alkyl, allyl or aralkyl with 1 to 22 C atoms such as, for example, methoxy acrylate, ethoxy, lauroxy or stearoxypolyoxyethylene, octoxy acrylate, stearoxy or allyloxypolyoxyethylene-polyoxypropylene or nonylphenoxypolyoxyalloxyalloxy. Aminoalkyl acrylates such as, for example, N, N-dimethylaminoethyl acrylate or N, N'-dimethylaminopropyl acrylate can also be used.

In the case where in the compounds of the general formula (VI) X represents NH, in addition to acrylamide, substituted acrylamides can also be used, such as, for example, acrylic acid tert-butylamide, acrylic acid isopropylamide, N- acid amide methylolacrylic acid, N-butoxymethyl acrylamic acid amide, Nisobutyloxymethyl acrylic acid amide, N, N'-dimethylaminopropylacrylic acid amide, acrylic acid phenylamide and 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS) as well as their salts. If X represents NR, then, for example, N, N'-dimethylamide of acrylic acid is used. Mixtures of the individual acrylic acid esters with each other and with the acrylic acid amides are also according to the invention.

As compounds of the general formula (VII), the following monoisocyanates are preferably taken into account: methyl isocyanate, ethyl isocyanate, propyl isocyanate, n-butyl isocyanate, tert-butyl isocyanate, isobutyl isocyanate, pentyl isocyanate, isocyanate neopentyl, 2-ethylhexyl isocyanate, octyl isocyanate, cyclohexyl isocyanate, phenyl isocyanate, toloyl isocyanate, 1-naphthyl isocyanate, 2-naphthyl isocyanate, stearyl isocyanate as well as monoaducts known as isocyanate isocyanate US document

6,420,466 of the general formula OCN-C6H3 (CH3) -NHCOO-R8, wherein R8 preferably represents a C1-C22 alkyl, aryl, C7-C12 aralkyl or C5-C12 cycloalkyl moiety, a C1-C22 alkoxy, cycloalkoxyl moiety C5-C12 or C7-C12 polyoxyalkylene aralkoxy, in the case of the oxyalkylene moiety of ethylene oxide, propylene or butylene, including mixtures thereof, and parts of the oxyalkylene moiety may be substituted by styrene oxide or a polyester initiated with C1-alkanol C22, C5-C12 cycloalkane, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy based on, for example, C1-C18 hydroxycarboxylic acids or lactones such as, for example, β-propiolactone, δ-valerolactone, ε-caprolactone or ε-caprolactone substituted with C1-C6 alkyl, including mixtures thereof. Individual monoisocyanates can also be used in mixtures.

The addition reaction between the compounds of general formula (V) and (VI) is preferably carried out at a reaction temperature of from 60 to 100 ° C, especially preferably from 70 to 90 ° C. In this regard the ratio between (V) and (VI) is selected in such a way that for 1 mol of compound (V) when in compound (II) R1 represents H, 1.8 moles to 2.2 are preferably used moles, especially preferably from 1.9 moles to 2.1 moles, and most especially preferably 2 moles of the compound of the general formula (VI) and for the case in which in the compound (II) R 1 represents - ( CH2) 2-CO-X-R5, preferably 3.8 moles to 4.2 moles, especially preferably 3.9 moles to 4.1 moles, and most preferably 4 moles of compound (VI) . In the case where in compound (II) R1 = - (CH2) 2-CO-X-R5, esters and amides of acrylic acid can be added simultaneously or successively individually or in mixtures to compound (V). The reaction can be carried out in the presence or absence of solvents. Suitable solvents are all aliphatic, aromatic, protic and aprotic solvents such as, for example, methoxypropyl acetate, cyclohexane, toluene, xylene, high boiling alkylbenzoles or isoparaffins, N-methylpyrrolidone or N-ethylpyrrolidone, but also alcohols such as ethanol, propanol, i-butanol or glycols such as, for example, butyl glycol. Mixtures of solvents can also be used.

For the case where in the compound of general formula (II) R1 represents CONH-R ', representing R' R8 or C6H3 (CH3) -NHCOO-R8, at a reaction temperature of from 50 to 100 ° C, especially preferably from 60 to 80 ° C, 1 mol of the adduct of compound (V) and (VI) are preferably added from 1.8 mol to 2.2 mol, especially preferably from 1.9 mol to 2.1 mol, of very particularly preferably 2 moles of the compound of the general formula (VII). The monoisocyanates can be the same or different. This reaction can be carried out with or without catalyst. Suitable catalysts are both organic tin compounds such as, for example, dibutyltin dilaurate (DBTL) and tertiary amines such as, for example, diazabicyclo [2.2.2] octane (DABCO). The reaction can be carried out with or without solvent. Suitable solvents are all aliphatic, aromatic and aprotic solvents such as, for example, methoxypropyl acetate, cyclohexane, toluene, xylene, high boiling alkylbenzoles or isoparaffins,

N-methylpyrrolidone or N-ethylpyrrolidone. Mixtures of solvents can also be used.

The compounds of general formula (III)

R5-X-CO- (CH2) 2-NR1-R2- [Y-R3-Y-R4] to-Y-R6 (III)

where R1 represents H, (CH2) 2-CO-X-R5 or CONH-R ’and R’ represents R8 or C6H3 (CH3) -NHCOO-R8,

they can be produced, for example, by reacting one or more compounds of the general formula (VIII):

H2N-R2- [Y-R3-Y-R4] to-Y-R6 (VIII)

wherein R2, R3 and R4 independently of each other represent a C2-C40 alkylene, C3-C40 alkenylene, C5-C40 cycloalkylene, arylene, C7-C40 aralkylene or polyoxyalkylene moiety, being in the case of the ethylene oxide oxyalkylene moiety, propylene or butylene, including mixtures thereof, and parts of the oxyalkylene moiety may be substituted by styrene oxide, or a polyester moiety based on, for example, C1-C18 hydroxycarboxylic acids or lactones such as, for example, β-propiolactone, δ -valerolactone, ε-caprolactone or ε-caprolactone substituted with C1-C6 alkyl, including mixtures thereof,

Y represents one or more of the following groups COO, OCO, NHCO, CONH, NHCOO, OOCNH, NHCONH, and

a represents a number from 1 to 19, and

R6 represents a C1-C30 alkyl, C3-C22 alkenyl, hydroxyalkyl, C4-C13 cycloalkyl, aryl or C7-C12 aralkyl moiety,

with one or more compounds of the general formula (VI):

R5-X-CO-CH = CH2 (VI)

wherein R5 represents H, a C1-C22 alkyl, aryl, C7-C12 aralkyl, C5-C12 cycloalkyl, hydroxyalkyl or N, N'dialkylamino moiety, a hydroxyl, C1-C22 alkoxy, C5-C12 alkoxy or C7 aralkoxy moiety -C12-polyoxyalkylene, in the case of the oxyalkylene moiety of ethylene oxide, propylene or butylene, including mixtures thereof, and parts of the oxyalkylene moiety may be substituted by styrene oxide or a polyester initiated with C1-C22 alkanol, C5 cycloalkane- C12, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy based on, for example, C1-C18 hydroxycarboxylic acids or lactones such as, for example, β-propiolactone , δvalerolactone, ε-caprolactone or ε-caprolactone substituted with C1-C6 alkyl, including mixtures thereof,

X represents O, NH or NR9, and

R9 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl, hydroxyalkyl, C5-C12 cycloalkyl moiety,

and then the product is reacted if necessary with compounds of general formula (VII):

R’-NCO (VII)

in which R ’represents R8 or -C6H3 (CH3) -NHCOO-R8 and

R8 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl or C5-C12 cycloalkyl, a C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy moiety, being treated in the case of the oxyalkylene oxide moiety of ethylene, propylene or butylene, including mixtures thereof, and parts of the oxyalkylene moiety are substituted where appropriate by styrene oxide, a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkane or C7-C12 aralcanol or a C1 alkoxy initiated polyester -C22, C6-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy based on, for example, C1-C18 hydroxycarboxylic acids or lactones such as, for example, β-propiolactone, δ-valerolactone, ε-caprolactone or ε-substituted caprolactone with C1-C6 alkyl, including mixtures thereof.

The intermediate compounds of the general formula (VIII) are produced under conditions known to those skilled in the art and can be obtained, for example, by reacting a mixture of mono and polycarboxylic acids, preferably dicarboxylic acids, and / or dicarboxylic acid anhydrides, with diamines, preferably at temperatures of from 100 to 250 ° C, especially preferably from 140 to 200 ° C with water separation. Preferably the compounds of the general formula (VIII) can be produced by first reacting the dicarboxylic acid and / or the dicarboxylic acid anhydride with the diamine at temperatures from 100 to 250 ° C, especially preferably from 140 to 200 ° C with water separation to give the product of

condensation of the general formula (V) with an amine index of preferably from 5 to 180 and especially preferably from 15 to 100, with respect to 100% active substance, and then reacting at temperatures of from 100 to 250 ° C, especially preferably from 140 to 200 ° C, the compound (V) with the monocarboxylic acid with water separation to give the compound (VIII), this condensation product having an amine index of preferably from 3 to 80 and especially preferably from 8 to 50, with respect to 100% active substance. The ratio of diamine with respect to polycarboxylic acid with respect to monocarboxylic acid amounts to 3 with respect to 2 with respect to 1 with 20 with respect to 19 with respect to 1, especially preferably with 3 with respect to 2 with respect to 2 with respect to 1 to 8 with respect to 7 with respect to 1.

The mono or polycarboxylic acids can be partially substituted by mono or diisocyanates and the diamines partially by diols, then there may be ester, urethane and / or urea groups in addition to the preferred amide groups in the compounds of the general formula (VIII).

In the case of monocarboxylic acids, they are aliphatic, linear and branched, saturated, mono to polyunsaturated carboxylic acids such as, for example, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, caproic acid , enantic acid, caprylic acid, pelargonic acid, caprinic acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachidic acid, behenic acid, lignoceric acid, acid cerotic, melisic acid, lauroleic acid, myristoleic acid, palmitoleic acid, petroslelenic acid, oleic acid, elaidinic acid, vaccenic acid, erucic acid, linoleic acid, linolenic acid, arachidonic acid, clupanodonic acid, ricinoleic acid, α-eleostearic acid, acid α-parinaric, co-oil fatty acid co, palm kernel oil fatty acid, coconut oil / palm seed fatty acid, palm oil fatty acid, cottonseed fatty acid, peanut oil fatty acid, soybean oil fatty acid, acid grade sunflower oil, acid grade rapeseed oil and acid grade sebum. Also used are ketocarboxylic acids such as, for example, liquenic acid, as well as aromatic monocarboxylic acids such as, for example, benzoic acid. As representatives of hydroxycarboxylic acids, for example, glycolic acid, 5-hydroxyvaleric acid, 6-hydroxycaproic acid, ricinoleic fatty acid, 12-hydroxystearic acid, 12-hydroxidedecanoic acid, 5-hydroxidedecanoic acid, 5-hydroxidecanoic acid or acid are mentioned. 4-hydroxidecanoic. Mixtures of the monocarboxylic acids can also be used.

The addition reaction between the compounds of general formulas (VIII) and (VI) is preferably carried out at a reaction temperature of from 60 to 100 ° C, especially preferably from 70 to 90 ° C. In this regard the ratio between the compounds of general formulas (VIII) and (VI) is preferably selected such that for 1 mol of compound of general formula (VIII), when R 1 represents H, 0.8 is used moles to 1.2 moles, especially preferably 0.9 moles to 1.1 moles, and most particularly preferably 1 mole of the compound of the general formula (VI) and in the case where in the compound of the formula general

(III) R1 represents (CH2) 2-CO-X-R5, preferably from 1.8 moles to 2.2 moles, especially preferably from 1.9 moles to 2.1 moles, and most particularly preferably 2 moles of compound (VI). In the case where in compound (III) R1 represents (CH2) 2-CO-X-R5, the amides and esters of acrylic acid can be added simultaneously or successively individually or in mixtures to the compound of general formula (VIII) . The reaction can be carried out with or without solvent. Suitable solvents are all aliphatic, aromatic, protic and aprotic solvents such as, for example, methoxypropyl acetate, cyclohexane, toluene, xylene, high boiling alkylbenzoles or isoparaffins. Also suitable are N-methylpyrrolidone or N-ethylpyrrolidone, but also alcohols such as ethanol, propanol, i-butanol or glycols such as, for example, butyl glycol. Mixtures of solvents can also be used.

In the case where in the compounds of formula (III) R1 represents CONH-R 'with R' = R8 or C6H3 (CH3) -NHCOOR8, preferably at a reaction temperature of preferably from 50 to 100 ° C, especially preferably 60 to 80 ° C for 1 mole of the adduct of the compounds of general formulas (VIII) and (VI) are preferably added from 0.8 moles to 1.2 moles, especially preferably from 0.9 moles to 1.1 moles , and most especially preferably 1 mol of the compound of general formula (VII). The monoisocyanates can be the same or different. The reaction can be carried out with or without catalyst. Suitable catalysts are both organic tin compounds such as, for example, DBTL as well as tertiary amines such as, for example, DABCO. This reaction can be carried out with or without solvent. Suitable solvents are all aliphatic, aromatic and aprotic solvents such as, for example, methoxypropyl acetate, cyclohexane, toluene, xylene, high boiling alkylbenzoles or isoparaffins, N-methylpyrrolidone or Netylpyrrolidone. Mixtures of solvents can also be used.

The compounds of general formula (IV)

R6-Y- [R4-Y-R3-Y] a-R2-NR1- (CH2) 2-CO-X-R7-X-CO- (CH2) 2-NR1-R2- [Y-R3-Y- R4] aY-R6 (IV)

with R1 = -H, - (CH2) 2-CO-X-R5, -CONH-R ’with R’ = R8 or -C6H3 (CH3) -NHCOO-R8

they can be produced, for example, by reacting one or more compounds of the general formula (VIII): H2N-R2- [Y-R3-Y-R4] aY-R6 (VIII) in which R2, R3 and R4 independently represent one another a C2-C40 alkylene, C3-C40 alkenylene, C5-C40 cycloalkylene, arylene, C7-C40 aralkylene or polyoxyalkylene radical, in the case of the oxyalkylene moiety of ethylene oxide, propylene or butylene, including mixtures thereof, and parts of the remainder oxyalkylene may be substituted by styrene oxide, or a polyester moiety based on, for example, C1-C18 hydroxycarboxylic acids or

lactones such as, for example, β-propiolactone, δ-valerolactone, ε-caprolactone or ε-caprolactone substituted with C1-C6 alkyl, including mixtures thereof, Y represents one or more of the following groups COO, OCO, NHCO, CONH, NHCOO, OOCNH, NHCONH, and a represents a number from 1 to 19, and R6 represents a C1-C30 alkyl, C3-C22 alkenyl, hydroxyalkyl, C4-C13 cycloalkyl, aryl or C7-C12 aralkyl moiety, with one or more compounds of the general formula (IX):

H2C = HC-CO-X-R7-X-CO-CH = CH2 (IX) in which R7 represents a C1-C18 alkylene, C3-C18 alkenylene, C5-C12 cycloalkylene, arylene, C7-C15 aralkylene or polyoxyalkylene radical , in the case of the oxyalkylene moiety of ethylene, propylene or butylene oxide, including mixtures thereof, and parts of the oxyalkylene moiety may be substituted by styrene oxide, or a polyester moiety based on, for example, C1-C18 hydroxycarboxylic acids or lactones such as, for example,

β-propiolactone, δ-valerolactone, ε-caprolactone or ε-caprolactone substituted with C1-C6 alkyl, including mixtures thereof, X represents O, NH or NR9, and R9 represents a C1-C22 alkyl moiety, aryl, C7 aralkyl -C12, hydroxyalkyl, C5-C12 cycloalkyl and then the product is reacted if necessary

(a) with one or more compounds of general formula (VI):

R5-X-CO-CH = CH2 (VI)

wherein R5 represents H, a C1-C22 alkyl, aryl, C7-C12 aralkyl, C5-C12 cycloalkyl, hydroxyalkyl or N, N'dialkylamino moiety, a hydroxyl, C1-C22 alkoxy, C5-C12 alkoxy or C7 aralkoxy moiety -C12-polyoxyalkylene, in the case of the oxyalkylene moiety of ethylene oxide, propylene or butylene, including mixtures thereof, and parts of the oxyalkylene moiety may be substituted by styrene oxide or a polyester initiated with C1-C22 alkanol, C5 cycloalkane- C12, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy based on, for example, C1-C18 hydroxycarboxylic acids or lactones such as, for example, β-propiolactone , δ-valerolactone, ε-caprolactone or ε-caprolactone substituted with C1-C6 alkyl, including mixtures thereof,

X represents O, NH or NR9, and

R9 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl, hydroxyalkyl, C5-C12 cycloalkyl moiety, and / or

(b) one or more compounds of the general formula (VII):

R’-NCO (VII)

in which R ’represents R8 or -C6H3 (CH3) -NHCOO-R8 and

R8 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl or C5-C12 cycloalkyl, a C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy moiety, being treated in the case of the oxyalkylene oxide moiety of ethylene, propylene or butylene, including mixtures thereof, and parts of the oxyalkylene moiety are substituted where appropriate by styrene oxide, a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkane or C7-C12 aralcanol or a C1 alkoxy initiated polyester -C22, C6-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy based on, for example, C1-C18 hydroxycarboxylic acids or lactones such as, for example, β-propiolactone, δ-valerolactone, ε-caprolactone or

ε-caprolactone substituted with C1-C6 alkyl, including mixtures thereof.

In the case of the compounds of the general formula (IX), when X represents O, it is preferably linear, branched or cycloaliphatic diols with 2 to 36 C atoms, such as, for example, ethanediol diacrylate, diacrylate of 1,3-butanediol, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,10-decanediol diacrylate or 2,2-dimethyl-1,3-propanediol diacrylate. Also included are oligo and polyoxyalkylene diacrylates with from 10 to 100 C atoms such as, for example, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, polyacryloxyethylene acrylate , polyoxybutylene diacrylate, polyoxyethylene-polyoxybutylene diacrylate, polyoxypropylene-polyoxybutylene diacrylate, polyoxyethylene-polyoxypropylene-polyoxyethylene diacrylate as well as urethane diacrylate, bisphenol A or epoxy bisphenol A and 1-diaphatyl epoxy diacrylate 15 alkoxy, ethoxylated or propoxylated 2,2-dimethyl-1,3-propanediol diacrylate groups. Also available as compounds of the general formula (IX) are polyester diacrylates, such as, for example, polyproctone and / or valerolactone-based polylactone diacrylates and mixed polyether-polyester diacrylates.

For the case where X represents NH, bisacrylic acid amides are preferably used such as, for example, N, N’-methylenebisacrylic acid amide or N, N’ - (1,2-dihydroxyethylene) bisacrylic acid amide. Diacrylates can also be used in mixtures with each other or together with the amides of bisacrylic acid, reduced amounts of triacrylates such as, for example, trimethylolpropane triacrylate or alkoxylated trimethylolpropane triacrylate can also be used.

The addition reaction between the compounds of the general formula (VIII) and (IX) is preferably carried out at a reaction temperature of from 60 to 100 ° C, especially preferably from 70 to 90 ° C. In this regard the ratio between the compounds of general formulas (VIII) and (IX) is preferably selected such that for 1 mol of the compound of general formula (IX), when R 1 represents H in this case, preferably 1, 8 moles to 2.2 moles, especially preferably 1.9 moles to 2.1 moles, and most particularly preferably 2 moles of compound (VIII). When in the compound of general formula (IV) R1 represents (CH2) 2-CO-X-R5, preferably for 1 mole of the adduct of the compounds of general formulas

(VIII)

 and (IX) at a reaction temperature of preferably from 60 to 100 ° C, especially preferably from 70 to 90 ° C, preferably from 1.8 moles to 2.2 moles, especially preferably from 1.9 moles to 2, are used , 1 mole, and most especially preferably 2 moles of compound (VI). The reaction can be carried out with or without solvent. Suitable solvents are all aliphatic, aromatic, protic and aprotic solvents such as, for example, methoxypropyl acetate, cyclohexane, toluene, xylene, high boiling aromatic compounds or isoparaffins. Also suitable are N-methylpyrrolidone or Netylpyrrolidone, but also alcohols such as ethanol, propanol, i-butanol or glycols such as, for example, butyl glycol. Mixtures of solvents can also be used.

For the case where in the compound of general formula (IV) R1 represents CONH-R 'with R' = R8 or -C6H3 (CH3) -NHCOO-R8, at a reaction temperature of preferably from 50 to 100 ° C, of especially preferably from 60 to 80 ° C for preferably 1 mole of the adduct of the compounds of general formulas

(VIII)

 and (IX), preferably from 1.8 moles to 2.2 moles, especially preferably from 1.9 moles to 2.1 moles, and most particularly preferably 2 moles of the compound of general formula (VII) are added. The monoisocyanates can be the same or different. This reaction can be carried out with or without catalyst. Suitable catalysts are both organic tin compounds such as, for example, DBTL, and tertiary amines such as, for example, DABCO. This reaction can be carried out with or without solvent. Suitable solvents are all aliphatic, aromatic and aprotic solvents such as, for example, methoxypropyl acetate, cyclohexane, toluene, xylene, high boiling alkylbenzoles or isoparaffins, N-methylpyrrolidone or N-ethylpyrrolidone. Mixtures of solvents can also be used.

Furthermore, the present invention relates to the use of the amide-containing polymers according to the invention or of the amide-containing polymers obtained by the process according to the invention as rheology control additives, in particular in solvent-containing and solvent-free lacquers. based on binders such as, for example, polyurethanes (1K and 2K), polyacrylates, polyester, alkyd and epoxy resins, PVC plastisols and organosols, epoxy base coatings and unsaturated polyester resins. Lacquers can also be understood as nail polishes, as described, for example, in US Patent 6,156,325.

The amount used of the amide-containing polymers according to the invention is usually 0.05 to 5.0% by weight of active substance, preferably 0.1 to 3.0% by weight of active substance and especially preferably 0.2 to 2.0% by weight of active substance, based on the weight of the total formulation.

A further object of the invention are hardened and non-hardened polymeric compositions containing one

or several of the amide-containing polymers according to the invention or of the amide-containing polymers obtained by the process according to the invention.

Examples

Example 1:

In a 3-liter 1-liter flask with agitator, water separator and thermometer, 226.4 g (0.4 mol) of Pripol ™ 1006 dimeric acid (dimerized, hydrated fatty acid, Uniqema), 69.6 g are successively weighed (0.6 moles) of hexamethylenediamine and 127 g of Shellsol A (high boiling aromatic hydrocarbon, Shell Chemicals) and slowly heated to 170 ° C. Water that is slowly released during the reaction is azeotropically separated by the water separator. The condensation product has an amine number of about 54. The reaction mixture is then cooled to 50 ° C.

Example 2:

In a 3-liter 1-liter flask with agitator, water separator and thermometer, 226.4 g (0.4 mol) of the dimeric acid Pripol ™ 1006 (Uniqema), 55.7 g (0.48 mol) are successively weighed of hexamethylenediamine and 121 g of Shellsol D40 (dearomatized hydrocarbon, Shell Chemicals) and slowly heated to 170 ° C. Water that is slowly released during the reaction is azeotropically separated by the water separator. The condensation product has an amine index of approximately 23. The reaction mixture is then cooled to 50 ° C.

Example 3:

In a 3-liter 1-liter flask with stirrer, water separator and thermometer, 226.4 g (0.4 mol) of the dimeric acid Pripol ™ 1006 (Uniqema), 69.6 g (0.6 mol) are successively weighed of hexamethylenediamine and 152 g of Shellsol D40 and slowly heated to 170 ° C. Water that is slowly released during the reaction is azeotropically separated by the water separator. The condensation product has an amine index of about 51. Next, 57.6 g (0.2 mol) of talol fatty acid (mixture of monocarboxylic acids with a high content of oleic and linoleic acid and about 2 are added % of resin acids (abietic acid), Arizona Chemical GmbH) and the water that is released during this reaction is azeotropically separated by the water separator. This condensation product has an amine index of approximately 23. The reaction mixture is then cooled to 50 ° C.

Example 4:

In a 3-liter 1-liter flask with stirrer, water separator and thermometer, 232 g (0.4 mol) of the dimeric acid Pripol ™ 1017 (dimerized, unsaturated fatty acid, Uniqema), 55.7 g (0) are successively weighed , 48 moles) of hexamethylenediamine and 133 g of Cobersol B 60 (mixture of isoparaffinic hydrocarbons, C9-C12 isoalkanes, Cölner Benzin-Raffinerie) and slowly heat to 170 ° C. Water that is slowly released during the reaction is azeotropically separated by the water separator. The condensation product has an amine index of approximately 22. Next, 22.8 g (0.08 mol) of stearic acid are added and the water released during this reaction is azeotropically separated by the water separator. This condensation product has an amine index of approximately 10.5. The reaction mixture is then cooled to 50 ° C.

Example 5:

In a 3-liter 1-liter flask with stirrer, water separator and thermometer 214.5 g (0.375 mol) of Empol® 1062 dimeric acid (distilled dimerized fatty acid, partially hydrated, Cognis), 68.1 g are weighed successively (0.5 mol) of m-xylylenediamine and 121 g of Cobersol B 60 and slowly heat to 170 ° C. Water that is slowly released during the reaction is azeotropically separated by the water separator. The condensation product has an amine number of about 35. The reaction mixture is then cooled to 50 ° C.

Example 6:

In a 3-liter 1-liter flask with stirrer, water separator and thermometer, 146 g (1 mol) of adipic acid, 180 g (1.25 mol) of octamethylenediamine and 140 g of Shellsol A are weighed and slowly heated up to 170 ° C. Water that is slowly released during the reaction is azeotropically separated by the water separator. The condensation product has an amine number of about 63. The reaction mixture is then cooled to 50 ° C.

Example 7:

In a 500 ml 3-mouth flask with agitator, reflux condenser and thermometer are weighed successively

150.9 g (0.075 mol) of the condensation product of example 1 and 17 g (0.15 mol) of N-isopropylacrylamide and heated to 80 ° C. The reaction mixture is stirred for 3 h. The product is then diluted with i-butanol to a solids content of 40%.

Example 8:

143.4 g (0.03 mol) of the condensation product of example 2 and 13 g (0.06 mol) of isodecyl acrylate are weighed successively in a 500 ml 3-neck flask with stirrer, reflux condenser and thermometer and they are heated to 80 ° C. The reaction mixture is stirred for 3 h. The product is then diluted with i-butanol to a solids content of 40%.

Example 9:

143.4 g (0.03 mol) of the condensation product of example 2 and 16 g (0.06 mol) of polyoxyethylene acrylate are weighed successively in a 500 ml 3-neck flask with stirrer, reflux condenser and thermometer 200 (Blemmer® AE 200, NOF) and heated to 80 ° C. The reaction mixture is stirred for 3 h. The product is then diluted with i-butanol to a solids content of 40%.

Example 10:

143.8 g (0.06 mol) of the condensation product of example 3 and 15 g (0.03 mol) of polyoxyethylene diacrylate are successively weighed in a 500 ml 3-neck flask with stirrer, reflux condenser and thermometer 400 (Sartomer ™ 344, Cray Valley) and heated to 80 ° C. The reaction mixture is stirred for 3 h. The product is then diluted with i-butanol to a solids content of 40%.

Example 11:

In a flask of 3 mouths of 500 ml with agitator, reflux condenser and thermometer, 143.8 g (0.06 mol) of the condensation product of example 3 and 4.6 g (0.03 mol) of N are successively weighed , N'-methylenebisacrylamide and heated to 80 ° C. The reaction mixture is stirred for 3 h. The product is then diluted with i-butanol to a solids content of 40%.

Example 12:

In a 500 ml 3-neck flask with stirrer, reflux condenser and thermometer, 154.97 g (0.03 mol) of the condensation product of example 4 and 18 g (0.03 mol) of polyoxyethylene acrylate are successively weighed 400 (Blemmer® AE 400, NOF) and heated to 80 ° C. The reaction mixture is stirred for 3 h. The product is then diluted with i-butanol to a solids content of 40%.

Example 13:

In a 500 ml 3-neck flask with agitator, reflux condenser and thermometer, 154.97 g (0.03 mol) of the condensation product of example 4 and 9.7 g (0.03 mol) of acrylate are successively weighed of stearyl and heated to 80 ° C. The reaction mixture is stirred for 3 h. The product is then diluted with i-butanol to a solids content of 40%.

Example 14:

In a 500 ml 3-neck flask with stirrer, reflux condenser and thermometer, 154.97 g (0.03 mol) of the condensation product of example 4 and 12.5 g (0.03 mol) of acrylate are successively weighed of lauroxypolyoxyethylene 200 (Blemmer® ALE 200, NOF) and heated to 80 ° C. The reaction mixture is stirred for 3 h. Then 9 g (0.03 mol) of stearyl isocyanate are added and stirred for a further 2 h at 80 ° C. The product is then diluted with i-butanol to a solids content of 30%.

Example 15:

In a 500 ml 3-neck flask with stirrer, reflux condenser and thermometer, 153.77 g (0.05 mol) of the condensation product of Example 5 and 34.4 g (0.1 mol) of Tone are successively weighed ™ M 100 (addition product of hydroxyethyl acrylate with 2 moles of ε-caprolactone, DOW) and heated to 80 ° C. The reaction mixture is stirred for 3 h. The product is then diluted with i-butanol to a solids content of 30%.

Example 16:

82.86 g (0.05 mol) of the condensation product of example 6 and 24 g (0.1 mol) of lauryl acrylate are successively weighed in a 500 ml 3-neck flask with stirrer, reflux condenser and thermometer and they are heated to 80 ° C. The reaction mixture is stirred for 3 h. Then, 24.8 g (0.1 mol) of the isocyanate prepolymer of formula OCN-C6H4 (CH3) -NHCOOC4H9 of US 6,420,466 is added and stirred for

5 2 h more at 80 ° C. The product is then diluted with i-butanol to a solids content of 30%.

Application examples

White lacquer formulation: Degalan white lacquer, 28% binder, 20% TiO2

Degalan® LP 64/12, 35% in Shellsol A (thermoplastic acrylate, dissolved in 35% in Shellsol A, Röhm 34.4

GmbH)

Disperbyk® 110 0.6

Kronos 2160 (TiO2) 20

Dispersion: 30 min. Dispermat, 40ºC, 18 m / s circumferential speed (8000 rpm, 4.5 cm Teflon disk) 10 glass beads 1 mm 1: 1 with grinding material

Degalan® LP 64/12, 35% in Shellsol A 45

Dosage of the additive: 1% by weight of active substance, based on the weight of the total composition

Processing: add the additive with stirring to the Dispermat, 2.5 cm serrated disc, 1000 rpm, 2 min.

15 Final check: rheological efficacy check in the form of the lift limit. To do this, additive lacquer systems are applied with the 50 - 500 μm and 550 - 1000 μm level scraper on BYK Gardner 2801 contrast cards with an automatic application bench of BYK Gardner (speed 3 cm / s). The contrast cards are dried hanging vertically. The flow resistance is measured in wet in μm. This is a measure of rheological effectiveness. The results are presented in table 1.

20 Table 1

Additive

Lift limit [μm]

Control (without additive)

90

Example 7

700

Example 8

900

Example 9

850

Example 10

850

Example 11

1000

Example 12

600

(continuation)

Additive

Lift limit [μm]

Example 13

900

Example 14

650

Example 15

650

Example 16

550

Claims (18)

1. Amide-containing polymers of general formula (I) AX-CO- (CH2) 2-NR1-R2- [Y-R3-Y-R4] aB (I) as well as its salts with carboxylic acids, esters of phosphoric acids and sulphonic acids, in which A represents R5 or R6 -Y- [R4-Y-R3-Y] b-R2-NR1- (CH2) 2-CO-X-R7 and B represents Y-R6 or NR1- (CH2) 2-CO-X-R5, and in which R1 represents H, (CH2) 2-CO-X-R5 and / or CONH-R 'with R' = R8 or -C6H3 (CH3) -NHCOO-R8, R2, R3, R4 and R7 independently of each other represent a C1-C40 alkylene moiety, C3-C40 alkenylene, cycloalkylene C5-C40, arylene, C7-C40 aralkylene or polyoxyalkylene or a polyester moiety, R5 represents H, a C1-C22 alkyl, aryl, C7-C12 aralkyl, C5-C12 cycloalkyl, N or N'dialkylamino moiety, a hydroxyl, C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-aralkoxy moiety polyoxyalkylene, or a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkanol, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy, R6 represents a C1-C30 alkyl, C3-C22 alkenyl, hydroxyalkyl, C4-C13 cycloalkyl, aryl or C7-C12 aralkyl moiety, R8 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl or C5-C12 cycloalkyl moiety, a C1-C22 alkoxy moiety, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy, a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkane or C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C6-C12 cycloalkoxy or C7-C12 aralkoxy-polyoxyalkylene, X represents the same or different O, NH or NR9 moieties, R9 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl, hydroxyalkyl, C5-C12 cycloalkyl moiety, Y represents one or more of the following groups COO, OCO, NHCO, CONH, NHCOO, OOCNH, NHCONH and a and b independently of each other represent a number from 1 to 19.

2.

Amide-containing polymers according to claim 1, wherein in the case that one or more of the radicals R2, R3, R4, R5, R7 and / or R8 contain a polyoxyalkylene fraction, this moiety or these moieties are (n ) consisting of units of ethylene oxide, propylene oxide and / or butylene oxide, arranged statistically or in blocks, and if necessary one or more of the units of ethylene oxide, propylene oxide and / or oxide of butylene are replaced by styrene units.

3.

Amide-containing polymers according to claim 1 or 2, wherein in the case that one or more of the radicals R2, R3, R4, R5, R7 and / or R8 comprise a polyester moiety, this moiety or these moieties are ( n) constituted (s) based on one or more C1-C18 hydroxycarboxylic acids or one or more lactones.

Four.

Amide-containing polymers according to claim 3, wherein the lactone or lactones are selected from the group comprising β-propiolactone, δ-valerolactone, ε-caprolactone and ε-caprolactone substituted with C1-C6 alkyl.

5.

Amide-containing polymers according to one or more of claims 1 to 4, wherein R1 represents H, (CH2) 2-CO-X-R5 and / or CONH-R ’with R’ = R8 or -C6H3 (CH3) -NHCOO-R8, R2 and R4 independently of each other represent a C2-C18 alkylene, C7-C15 aralkylene moiety, R3 represents a C2-C40 alkylene, C3-C40 alkenylene, C5-C40 cycloalkylene, arylene, C7-C40 aralkylene moiety, R5 represents H, a C1-C22 alkyl moiety, C5-C12 cycloalkyl, hydroxyalkyl, a hydroxyl moiety, C1-C22 alkoxy,

C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy, or a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkane, C7-C12 aralcanol or a C1-C22 alkoxylated polyester, C5-C12 cycloalkoxy, or C7-aralkoxy C12-polyoxyalkylene, R6 represents a C1-C30 alkyl moiety or a C3-C22 alkenyl moiety, R7 represents a C1-C18 alkylene moiety or a polyoxyalkylene moiety, R8 represents a C1-C22 alkyl moiety, X represents the same or different O or NH moieties, And represents one or more of the following NHCO and CONH groups, and a and b independently of each other represent a number from 1 to 19.

6.

Amide-containing polymers according to one or more of claims 1 to 5, wherein R1 represents H, (CH2) 2-CO-X-R5 and / or CONH-R ’with R’ = R8 or -C6H3 (CH3) -NHCOO-R8, R2 and R4 independently of each other represent a C2-C12 alkylene, C7-C12 aralkylene moiety, R3 represents a C2-C40 alkylene, C3-C40 alkenylene, C5-C40 cycloalkylene, arylene, C7-C40 aralkylene moiety, R5 represents H, a C1-C22 alkyl moiety, C5-C12 cycloalkyl, hydroxyalkyl, a hydroxyl moiety, C1-C22 alkoxy,

C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy, or a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkane, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12 aralkoxy-polyoxyalkylene, R6 represents a C12-C30 alkyl moiety or a C12-C22 alkenyl moiety, R7 represents a C1-C18 alkylene moiety or a polyoxyalkylene moiety, R8 represents a C1-C22 alkyl moiety, X represents the same or different O or NH moieties, And represents one or more of the following NHCO and CONH groups, and a and b independently of each other represent a number from 1 to 7.

7.

Amide-containing polymers according to one or more of claims 1 to 6, wherein R1 represents H, (CH2) 2-CO-X-R5 and / or CONH-R ’with R’ = R8 or -C6H3 (CH3) -NHCOO-R8, R2 and R4 independently of each other represent a C2-C8 alkylene, C7-C9 aralkylene moiety, R3 represents a C30-C40 alkylene, C30-C40 alkenylene, C30-C40 cycloalkylene, arylene, C30-C40 aralkylene moiety, R5 represents H, a C1-C22 alkyl moiety, C5-C12 cycloalkyl, hydroxyalkyl, a hydroxyl moiety, C1-C22 alkoxy,

C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy, or a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkane, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12 aralkoxy-polyoxyalkylene, R6 represents a C12-C20 alkyl moiety or a C12-C20 alkenyl moiety, R7 represents a C1-C18 alkylene moiety or a polyoxyalkylene moiety, R8 represents a C1-C22 alkyl moiety, X represents the same or different O or NH moieties, And represents one or more of the following NHCO and CONH groups, and a and b independently of each other represent a number from 1 to 7.

8.

Amide-containing polymers according to one or more of claims 1 to 7, characterized in that R1 represents hydrogen, CONH-C18H37 and / or CONH-C6H3 (CH3) -NHCOOC4H9, and / or R2 and R4 represent a hexamethylene, octamethylene or m moiety -xylene, and / or R3 represents a C34 moiety, and / or R6 represents a C17 alkyl moiety or a

C17 and / or X alkenyl moiety represents O or NH and / or Y represents CONH and / or NHCO and / or a and b represent in each case a number from 2 to 5. 9. Process for the production of polymers containing amide of general formula (I) AX-CO- (CH2) 2-NR1-R2- [Y-R3-Y-R4] aB (I) as well as its salts with carboxylic acids, esters of phosphoric acids and sulphonic acids, in which A represents R5 or R6 -Y- [R4-Y-R3-Y] b-R2-NR1- (CH2) 2-CO-X-R7 and B represents Y-R6 or NR1- (CH2) 2-CO-X-R5, and in those that R1 represents H, (CH2) 2-CO-X-R5 and / or CONH-R 'with R' = R8 or -C6H3 (CH3) -NHCOO-R8, R2, R3, R4 and R7 independently of each other represent a C1-C40 alkylene moiety, C3-C40 alkenylene, cycloalkylene C5-C40, arylene, C7-C40 aralkylene or polyoxyalkylene or represent a polyester moiety, R5 represents H, a C1-C22 alkyl, aryl, C7-C12 aralkyl, C5-C12 cycloalkyl, N or N'dialkylamino moiety, a hydroxyl, C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-aralkoxy moiety polyoxyalkylene, or a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkanol, C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy, R6 represents a C1-C30 alkyl, C3-C22 alkenyl, hydroxyalkyl, C4-C13 cycloalkyl, aryl or C7-C12 aralkyl moiety, R8 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl or C5-C12 cycloalkyl moiety, a C1-C22 alkoxy moiety, C5-C12 cycloalkoxy or C7-C12-polyoxyalkylene aralkoxy, a polyester initiated with C1-C22 alkanol, C5-C12 cycloalkane or C7-C12 aralcanol or a polyester initiated with C1-C22 alkoxy, C6-C12 cycloalkoxy or C7-C12 aralkoxy-polyoxyalkylene, X represents the same or different O, NH or NR9 moieties, R9 represents a C1-C22 alkyl, aryl, C7-C12 aralkyl, hydroxyalkyl, C5-C12 cycloalkyl moiety, Y represents one or more of the following groups COO, OCO, NHCO, CONH, NHCOO, OOCNH, NHCONH and a and b independently of each other represent a number from 1 to 19, characterized because (A) one or more compounds of general formulas (V) and (VIII) H2N-R2- [Y-R3-Y-R4] a-NH2 (V) H2N-R2- [Y-R3-Y-R4] a -YR (VIII) are reacted with one or more compounds of general formulas (VI) and (IX) R5-X-CO-CH = CH2 (VI) H2C = HC-CO-X-R7-X-CO-CH = CH2 (IX) forming compounds with R1 = hydrogen, used for 1 mol of NH2 groups in the compounds of general formulas (V) and (VIII) of 0, 8 to 1.2 moles of CH = CH2 groups in the compounds of formulas (VI) and (IX), and (B) in the case where R1 represents totally or partially (CH2) 2-CO-X-R5 and / or CONH-R ’, the compounds of step (A) are reacted with one or more compounds of general formulas (VI) and (VII) R5-X-CO-CH = CH2 (VI) R’-NCO (VII), using for 1 mol of NR1 groups in the compounds of step (A) up to 1.2 moles of compounds of general formula (VI) and / or (VII), and (C) for the case in which in the case of the compounds of general formula (I) it is acid salts Carboxylic esters of phosphoric acids and sulfonic acids, a reaction of the compounds of step (A) or (B) with carboxylic acids, esters of phosphoric acids and sulfonic acids takes place. 10. Process for the production of amide-containing polymers according to claim 9, wherein (A) one or more compounds of the general formula (V) H2N-R2- [Y-R3-Y-R4] a-NH2 (V) 10 are reacted with one or more compounds of the general formula (VI) R5-X-CO-CH = CH2 (VI) forming compounds with R1 = hydrogen, using for 1 mole of NH2 groups in compounds of general formula (V) of 0.8 to 1.2 moles of groups CH = CH2 in the compounds of formula (VI), and 15 (B) in the case where R1 represents wholly or partially (CH2) 2-CO-X-R5 and / or CONH-R ', the compounds of step (A) are reacted with one or more compounds of general formulas (VI) and (VII) R5-X-CO-CH = CH2 (VI) R'-NCO (VII), 20 being used for 1 mole of NR1 groups in the compounds of step (A) up to 1.2 moles of compounds of general formula (VI) and / or (VII), and (C) in the case where in the case of the compounds of the general formula (I) it is salts of carboxylic acids, esters of phosphoric acids and sulphonic acids, a reaction of the compounds of step (A) takes place. or (B) with carboxylic acids, esters of phosphoric acids and sulfonic acids. Method for the production of amide-containing polymers according to claim 9, wherein (A) one or more compounds of the general formula (VIII) H2N-R2- [Y-R3-Y-R4] to-YR6 (VIII) they are reacted with one or more compounds of the general formula (VI) R5-X-CO-CH = CH2 (VI) 30 forming compounds with R1 = hydrogen, using for 1 mol of NH2 groups in the compounds of the general formula (VIII) from 0.8 to 1.2 moles of groups CH = CH2 in the compounds of formula (VI), and (B) in the case where R1 represents totally or partially (CH2) 2-CO-X-R5 and / or CONH-R ’, the compounds of step (A) are reacted with One or more compounds of general formulas (VI) and (VII) R5-X-CO-CH = CH2 (VI) R’-NCO (VII), using for 1 mol of NR1 groups in the compounds of step (A) up to 1.2 moles of compounds of general formula (VI) and / or (VII), and (C) in the case where in the case of the compounds of the general formula (I) it is salts of carboxylic acids, esters of phosphoric acids and sulphonic acids, a reaction of the compounds of step (A) takes place. or (B) with carboxylic acids, esters of phosphoric acids and sulfonic acids. 12. Process for the production of amide-containing polymers according to claim 9, wherein (A) one or more compounds of the general formula (VIII) H2N-R2- [Y-R3-Y-R4] to-YR6 (VIII) They are reacted with one or more compounds of the general formula (IX) H2C = HC-CO-X-R7-X-CO-CH = CH2 (IX) forming compounds with R1 = hydrogen, used for 1 mol of NH2 groups in compounds of general formula (VIII) from 0.8 to 1, 2 moles of groups CH = CH2 in the compounds of formula (IX), and

(B)

 in the case where R1 represents totally or partially (CH2) 2-CO-X-R5 and / or CONH-R ', the compounds of step (A) are reacted with one or more compounds of general formulas (VI ) and (VII) R5-X-CO-CH = CH2 (VI)

R’-NCO (VII), with up to 1.2 moles of compounds of general formula (VI) and / or (VII) being used for 1 mole of NR1 groups in the compounds of step (A), and

(C)

 in the case in which in the case of the compounds of the general formula (I) it is salts of carboxylic acids, esters of phosphoric acids and sulfonic acids, a reaction of the compounds of step (A) or (B) takes place ) with carboxylic acids, esters of phosphoric acids and sulfonic acids.

13.

Process for the production of polymers containing amide according to one of claims 9 to 11, wherein the amount indicated in step (B) of the compounds of general formula (VI) is not used in step (B), but already in step (A) in addition to the amount indicated in step (A) of the compounds of general formula (VI).

14.

Process according to one or more of claims 9 to 13, wherein the reaction in step (A) is carried out at a temperature of from 60 to 100 ° C, preferably from 70 to 90 ° C.

fifteen.

Process according to one or more of claims 9 to 14, wherein the reaction in step (B), in the case of the reaction with compounds of general formula (VII), is carried out at a temperature of from 50 to 100 ° C, preferably from 60 to 80 ° C and in the case of the reaction with a compound of general formula (VI) at a temperature of from 60 to 100 ° C, preferably from 70 to 90 ° C.

16.

Use of the amide-containing polymers according to claims 1 to 8 or obtained by the process according to one of claims 9 to 15, as a rheology control additive.

17.

Use according to claim 16, wherein the rheology control additive is used in solvent-free lacquers and containing solvents based on binders such as polyurethanes (1K and 2K), polyacrylates, polyester, alkyd and epoxy resins, PVC plastisols and organosols, epoxy based coatings and unsaturated polyester resins.

18.

Use according to one of claims 16 or 17, wherein the rheology control additive is used in an amount of from 0.05 to 5.0% by weight of active substance, preferably 0.1 to 3 , 0% by weight of

active substance, especially preferably 0.2 to 2.0% by weight of active substance, with respect to the total weight of the composition in which the rheology control additive is used.

19.

Hardened and non-hardened polymeric compositions containing amide-containing polymers according to claims 1 to 8 or obtained by the process according to one of claims 9 to 15.